O-Toluidine → HCID 22941063, compound

HRID 342156Notes

Reaction equation

HRID 342156 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([NH:16][C@@H:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH:18]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:18][C@@H:17]([NH:16][C:14]([O:13][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:15])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 5049666Sodium triacetoxyborohydrideHCID 10420833(S)-tert-butyl 1-oxohexan-2-ylcarbamate

Product 1

HCID 22941063HCID 22941063, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 39, Step C, except using o-toluidine (0.32 mL, 3.00 mmol), 2(S)-(tert-butoxycarbonylamino)hexanal (0.538, 2.50 mmol), sodium triacetoxyborohydride (0.795 g, 3.75 mmol) in dichloroethane (10 mL) The crude product was purified by column chromatography to yield the title compound.

Workup

  1. customThe title compound was prepared
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8782a309aed94875ae01d76c6ecb8d1e
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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